Questionable Questing

The problem, imo, is with half-assing it. Tip jars are doomed to fail from what I've seen second hand, and all they do is make you feel bad/like a failure. If you want to give yourself a financial incentive to write, you have to give your readers a serious (but also reliable) incentive to support you financially. Just saying "feel free to donate but all content will remain free" is going to result in nobody donating.

Ah, okay but what about, "I wish I actually needed the money I'd get from writing"?

Money makes the world go round. You always need the money, even if you might not think you do

Hahaha, but it's a matter of opportunity cost, I guess. But instead, it's just "I gain more from doing nothing than spending time and effort trying to make money from writing", or something like that.

I guess it's not exactly about just how much money is gained, but an overall happiness, wealth, health, whatever else weighing system?

Oh yeah for sure. You have to weigh your options. I spent four years working retail/service industry and got to the point where it literally felt like my soul was being sucked out of my body. The 'career path' I saw myself taking was eventually becoming a manager at the store and just... sitting in that job forever and ever. And I hated that idea.

So I made writing work for me.

But if you're in better circumstances, then trying to make money from a hobby like writing might not make sense tbh.